3,4-dihydro-2H-pyran → HCID 59838331, compound

HRID 273370Notes

Reaction equation

HRID 273370 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:11]2)=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 819704-Bromo-3,5-dimethylphenolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 59838331HCID 59838331, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-3,5-dimethylphenol (10.5 g, 52.2 mmol), 3,4-dihydro-2H-pyran (8.83 g, 105 mmol) and pyridinium p-toluenesulfonate (2.64 g, 10.5 mmol) in dichloromethane (160 mL) was stirred at room temperature for 80 hrs. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane) to give the title compound (11.5 g, yield 77%) as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-440fb0438bfa4b4899c679e8538e1366
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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